GSK1104252A | 1001397-20-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: GSK1104252A
• 英文别名: 1-methylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate；propan-2-yl 4-[[7-(2-fluoro-4-methylsulfonylphenyl)-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidine-1-carboxylate
• CAS: 1001397-20-1
• 化学式: C₂₂H₂₇FN₄O₅S
• 分子量: 478.545
• InChiKey: HCCOWIAORWVUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-烯丙基-4,6-二氯嘧啶 在 sodium hydride 、 臭氧 、 三乙胺 、 甲基磺酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 GSK1104252A
  参考文献：
  名称：

  Discovery of 6,7-Dihydro-5H-pyrrolo[2,3-a]pyrimidines as Orally Available G Protein-Coupled Receptor 119 Agonists

  摘要：

  GPR119 is a 7-transmembrane receptor that is expressed in the enteroendocrine cells in the intestine and in the islets of Langerhans in the pancreas. Indolines and 6,7-dihydro-5H-pyrrolo[2,3-a]pyrimidines were discovered as G protein-coupled receptor 119 (GPR119) agonists, and lead optimization efforts led to the identification of 1-methylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (GSK1104252A) (3), a potent and selective GPR119 agonist. Compound 3 showed excellent pharmacokinetic properties and sufficient selectivity with in vivo studies supporting a role for GPR119 in glucose homeostasis in the rodent. Thus, 3 appeared to modulate the enteroinsular axis, improve glycemic control, and strengthen previous suggestions that GPR119 agonists may have utility in the treatment of type 2 diabetes.

  DOI：

  10.1021/jm301404a

文献信息

• METHODS FOR PREPARATION OF (4,6-DIHALO-PYRIMIDIN-5-YL)-ACETALDEHYDES
  申请人：SUZHOU JONATHAN NEW MATERIAL TECHNOLOGY CO., LTD.

  公开号：US20150368206A1

  公开（公告）日：2015-12-24

  This invention relates to the synthesis of chemical compounds and particularly to methods for the preparation of (4,6-dihalo-pyrimidin-5-yl)-acetaldehydes. The methods involve preparing a compound of the following general formula V from a compound of the following general formula IV through hydrolysis under the action of mercury dichloride and calcium carbonate, according to the following equation: wherein X is Cl or Br. The methods offer the benefits of use of highly available materials, high step yields, moderate reaction conditions, simply post-processing and purification, and suitability to industrialized production.

  这项发明涉及化学化合物的合成，特别是关于制备（4,6-二卤嘧啶-5-基）-乙醛的方法。该方法涉及通过在汞二氯化物和碳酸钙的作用下，通过水解将以下一般式IV的化合物制备成以下一般式V的化合物，如下方程所示：其中X为Cl或Br。该方法具有使用易得材料、高步骤产率、适度的反应条件、简单的后处理和纯化，以及适合工业化生产等优点。
• WO2008/8895
  申请人：——

  公开号：——

  公开（公告）日：——
• CHEMICAL COMPOUNDS
  申请人：KATAMREDDY Subba R.

  公开号：US20090318477A1

  公开（公告）日：2009-12-24

  The present invention relates to novel compounds that are useful in the treatment of metabolic disorders, particularly Type II diabetes mellitus and related disorders, and also to the methods for the making and use of such compounds.
• US8222261B2
  申请人：——

  公开号：US8222261B2

  公开（公告）日：2012-07-17
• US9278939B2
  申请人：——

  公开号：US9278939B2

  公开（公告）日：2016-03-08